Oakland Vacations from $377
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Your Oakland Vacation
From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.
The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Pittsburgh North Shore by IHG
North Shore
Save 100% on your flight
Price was $914, price is now $656 per person
$656
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Pittsburgh (PIT)
8.6/10 Excellent! (1,399 reviews)
Clean room. Convenient location. Heard some road noise through the night but if you’re a heavy sleeper it shouldn’t bother you. One of the elevators was out of order so it took a little longer to get to and from 8th floor. I would most likely stay again for location.
Reviewed on Mar 9, 2026
Placemakr Downtown Pittsburgh at The Pennsylvanian
Downtown Pittsburgh
Price was $921, price is now $691 per person
$691
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Pittsburgh (PIT)
8.2/10 Very Good! (71 reviews)
Room was clean , no curtains in the bedroom area which made sleeping after the sun came up hard but the room was great .
Reviewed on Feb 26, 2026
Wyndham Grand Pittsburgh Downtown
Downtown Pittsburgh
Price was $592, price is now $452 per person
$452
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Pittsburgh (PIT)
8.2/10 Very Good! (3,426 reviews)
Excellent overall experience. I was especially appreciative of free printing as I had to give a paper at a conference!
Reviewed on Mar 12, 2026
Hotel Indigo Pittsburgh University-Oakland by IHG
Oakland
Price was $843, price is now $645 per person
$645
per person
May 14 - May 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
8.6/10 Excellent! (1,007 reviews)
I’d stay here again!
Reviewed on Mar 13, 2026
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
4.5/5(2,251 area reviews)
Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.
Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $139 total per night from Apr 1 to Apr 2
$139 total
Apr 1 - Apr 2
Total with taxes and fees
9/10 Wonderful! (638 reviews)
This property is located in a great location within walking distance to the Cathedral of Learning,
Reviewed on Mar 13, 2026
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive Pittsburgh PA
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $145 total per night from Mar 22 to Mar 23
$145 total
Mar 22 - Mar 23
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
I’d stay here again!
Reviewed on Mar 13, 2026
The Oaklander Hotel, Autograph Collection
5130 Bigelow Boulevard Pittsburgh PA
Fully refundableReserve now, pay when you stay
$208 nightly
The price is $237 total per night from Mar 29 to Mar 30
$237 total
Mar 29 - Mar 30
Total with taxes and fees
9.2/10 Wonderful! (749 reviews)
Great
Reviewed on Mar 7, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Oakland
University of Pittsburgh
Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.
Carnegie Museum of Natural History
From rare jaguars to geological marvels and ancient fossils, you’ll find it all at this Pittsburgh institution, one of the country’s largest natural history museums.
Soldiers and Sailors Memorial Hall and Museum
You can spend an afternoon browsing the exhibits at Soldiers and Sailors Memorial Hall and Museum during your trip to Pittsburgh. Attend a sporting event or visit the shops in this family-friendly area.
Things to do
Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena
$93
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
$13
per adult
Pittsburgh: Beauty of the Burgh Bike Tour
$59
per adult
94% of travellers recommend
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- University of Pittsburgh
- University of Pittsburgh Medical Center
- The Nationality Rooms
- Petersen Events Center
- Cathedral of Learning
- Soldiers and Sailors Memorial Hall and Museum
- Carnegie Museum of Natural History
- Heinz Memorial Chapel
- Carnegie Museum of Art
- Phipps Conservatory
- Schenley Park
- Carnegie Mellon University
- Hunt Institute for Botanical Documentation
- Pittsburgh Opera
- Pittsburgh Vacations
- Shadyside Vacations
- Clemente Museum
- Strip District Vacations
- Contemporary Craft
- Market Square
- Visit Pittsburgh
- South Side Vacations
- Ppg Paints Arena
- Temple Sinai
- Senator John Heinz Regional History Centre
- Duquesne University
- Walnut Street
- Western Pennsylvania Sports Museum
- Visit Shadyside
- Roberto Clemente Bridge
- Chatham University
- Visit Bloomfield
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.